What Should Every Leader Ask Before Q4 Ends? The 3 Conversations That Will Define Your 2026

What should entrepreneurs focus on during National Entrepreneurship Month? Gratitude, and not the fluffy kind, I’m talking about a clear, strategic lens that helps real founders avoid burnout, reclaim energy, and build businesses that actually fuel them.

Entrepreneurship Isn’t Just Hustle, It’s Identity

November is National Entrepreneurship Month, a time to honor the 33.2 million entrepreneurs in the U.S. who’ve chosen a different path. The ones who didn’t wait for permission, who saw opportunity in the chaos, and who decided to build something of their own.

Entrepreneurship isn’t all Zen and innovation, its long nights, failed launches, doubting your own voice, and wondering if this was a crazy idea. As someone who’s built (and rebuilt) multiple businesses, I’ve come to realize that success doesn’t just come from action. It comes from alignment, and gratitude is one of the most underused, but most powerful tools in a founder’s toolbox.

2017 Josh

2017 Josh thought he knew so much, 2025 Josh would have lots to share with him, and gratitude would be at the top of the list.

Gratitude helps you regulate your energy, see failure as fuel, and return to service over ego. It brings you back to your “why”, which is often the first thing to fade when you’re buried in notifications and KPIs. In honor of National Entrepreneurship Month, I want to share what I call:

The Gratitude Stack: A 3 Part Entrepreneurial Reset

You don’t need another productivity hack; you need a moment to reset and realign with what really matters.

1. How Can Gratitude Help You Manage Your Energy as an Entrepreneur?

Running a business doesn’t just cost money, it costs energy, and most founders are overspending. Gratitude is how you track the ROI of your energy, not just where your time goes… but where your fire goes. When you’re grateful, you’re more attuned to what’s working (and what’s wearing you down).

Try this 3-minute daily check-in:

🔵 What gave me energy today?

🔵 What drained me?

🔵 What can I appreciate in that awareness?

Over time, you’ll start to see patterns. That client who lights you up vs. the one who doesn’t. The work that excites you vs. the stuff you procrastinate. And you can begin designing your business around what fuels you, not just what pays the bills. This is how you shift from grind mode to growth mode.

2. Why Should Entrepreneurs Be Grateful for Failure?

Because failure is feedback, and gratitude turns it into momentum. Entrepreneurs don’t fail because they’re weak, they fail because they take risks others won’t. But when failure happens, our instinct is to retreat, to hide it, bury it, or pretend it didn’t happen.

Gratitude asks you to sit with it and ask better questions:

🟠 What lesson did this failure teach me?

🟠 What clarity did I gain about my values or direction?

🟠 What doors opened because of it?

When I lost $1.3 million in one business venture, it nearly broke me. But that pain clarified my next move, it revealed what I wouldn’t compromise on again. And it made me a better leader, partner, and father. According to 2025 U.S. data, only 10% of startups succeed long-term. But 90% of entrepreneurs are self-made, that means they keep showing up, learning, and adjusting. Gratitude is what helps them keep going.

3. How Does Gratitude Anchor Entrepreneurs in Service (Not Just Sales)?

When you’re only focused on revenue, every ‘NO’ feels personal. But when you’re anchored in service, every ‘YES’ feels earned. Gratitude reminds you that entrepreneurship is bigger than you. It’s about the value you bring, the people you impact, and the difference your business makes, even if no one sees it today.

Ask yourself:

🔵 Who did I serve this week?

🔵 Where did I make someone feel seen, heard, or empowered?

🔵 Who do I need to thank for helping me lead better?

3. The Self Conversation: “What did I avoid… and why?”

Let’s get real: the hardest conversation is usually the one you avoid with yourself. This isn’t about judgment, it’s about honesty.

🟠 What decisions did you delay in 2025?

🟠 What conversations did you put off?

🟠 Where did fear, perfectionism, or burnout lead you to say “later” … and never come back?

Peter Drucker, the Austrian-American writer, consultant, and social philosopher widely known as the inventor of modern management, once said: “Follow effective action with quiet reflection. From the quiet reflection will come even more effective action.”

Josh and Rachel at a conference

Serving others brings my gratitude meter into focus.

It’s easy to lose sight of the human part of business, but that’s the part that lasts. The part that builds brand trust, client loyalty, and team culture. Metrics matter but meaning matters more.

Ready to Rewire Your Entrepreneurial Mindset?

The most successful entrepreneurs don’t just hustle harder, they reflect deeper, they reconnect to their mission, they learn from their failures, and they lead with gratitude.

This National Entrepreneurship Month, build your Gratitude Stack:

✅ Audit your energy

✅ Learn from what didn’t work

✅ Focus on service, not ego

And remember: your business doesn’t grow unless you grow. So be the entrepreneur who leads with clarity, not chaos. Happy National Entrepreneurship Month, my friends.

ICYMI

YOUmanize™ Your Brand Podcast | Can AI Fake Trust? Neuroscience Tips for Small Biz with John Assaraf

This episode features the legendary John Assaraf, brain science expert, serial entrepreneur, and founder of NeuroGym. John goes deep into the neuroscience of trust, AI, and how our ancient brains are trying to adapt to the fast-changing digital world.

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Josh & Rachel

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